CU20160096A7 - SOLID FORMS CRYSTALLINE 7 AND 8 OF (S) -ISOPROPIL 2 - ((S) - (((2R, 3R, 4R, 5R) -5- (2,4-DIOXO-3,4-DIHYDROPIRIMIDIN-1 (2H) -IL) -4-FLUORO-3-HIDROXI-4-METHYLETHYDRROFURAN-2-IL) METOXI) (FENOXI) PHOSPHORILAMINE) METHYL PROPANOATE (SOFOSBUVIR) - Google Patents

SOLID FORMS CRYSTALLINE 7 AND 8 OF (S) -ISOPROPIL 2 - ((S) - (((2R, 3R, 4R, 5R) -5- (2,4-DIOXO-3,4-DIHYDROPIRIMIDIN-1 (2H) -IL) -4-FLUORO-3-HIDROXI-4-METHYLETHYDRROFURAN-2-IL) METOXI) (FENOXI) PHOSPHORILAMINE) METHYL PROPANOATE (SOFOSBUVIR)

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Publication number
CU20160096A7
CU20160096A7 CUP2016000096A CU20160096A CU20160096A7 CU 20160096 A7 CU20160096 A7 CU 20160096A7 CU P2016000096 A CUP2016000096 A CU P2016000096A CU 20160096 A CU20160096 A CU 20160096A CU 20160096 A7 CU20160096 A7 CU 20160096A7
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CU
Cuba
Prior art keywords
dioxo
fluoro
solid forms
phosphorilamine
methylethydrrofuran
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CUP2016000096A
Other languages
Spanish (es)
Inventor
Melissa Jean Casteel
Kathleen Dashner
Fang Wang
Vahid Zia
Hyuk-Jun Jung
Mun Sik Seo
Bing Shi
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Gilead Pharmasset Llc
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Application filed by Gilead Pharmasset Llc filed Critical Gilead Pharmasset Llc
Publication of CU20160096A7 publication Critical patent/CU20160096A7/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Health & Medical Sciences (AREA)
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  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Epidemiology (AREA)
  • Biochemistry (AREA)
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  • Genetics & Genomics (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Communicable Diseases (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • AIDS & HIV (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La presente invención pertenece al sector de la industria farmacéutica, especialmente al desarollo de formas sólidas cristalinas del compuesto (S)-isopropil 2-((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihidropirimidin-1(2H)-il)-4-fluoro-3-hidroxi-4-metiltetrahidrofuran-2-il)metoxi)(fenoxi)fosforilamino)propanoato (Compuesto I) las cuales son útiles para limitar el establecimiento y la progresión de la infección por VHC. ESPACIO PARA FÓRMULA También se proporcionan procesos de fabricación y métodos de uso de las formas cristalinas, útiles en el tratamiento de VHC.The present invention belongs to the pharmaceutical industry sector, especially to the development of crystalline solid forms of compound (S) -isopropyl 2 - ((S) - (((2R, 3R, 4R, 5R) -5- (2,4 -dioxo-3,4-dihydropyrimidin-1 (2H) -yl) -4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl) methoxy) (phenoxy) phosphorylamino) propanoate (Compound I) which are useful for limit the establishment and progression of HCV infection. FORMULA SPACE Manufacturing processes and methods of use of crystalline forms, useful in the treatment of HCV, are also provided.

CUP2016000096A 2013-12-23 2016-06-22 SOLID FORMS CRYSTALLINE 7 AND 8 OF (S) -ISOPROPIL 2 - ((S) - (((2R, 3R, 4R, 5R) -5- (2,4-DIOXO-3,4-DIHYDROPIRIMIDIN-1 (2H) -IL) -4-FLUORO-3-HIDROXI-4-METHYLETHYDRROFURAN-2-IL) METOXI) (FENOXI) PHOSPHORILAMINE) METHYL PROPANOATE (SOFOSBUVIR) CU20160096A7 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361920371P 2013-12-23 2013-12-23
PCT/US2014/069123 WO2015099989A1 (en) 2013-12-23 2014-12-08 Crystalline forms of antiviral sofosbuvir analogues

Publications (1)

Publication Number Publication Date
CU20160096A7 true CU20160096A7 (en) 2016-11-29

Family

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CUP2016000096A CU20160096A7 (en) 2013-12-23 2016-06-22 SOLID FORMS CRYSTALLINE 7 AND 8 OF (S) -ISOPROPIL 2 - ((S) - (((2R, 3R, 4R, 5R) -5- (2,4-DIOXO-3,4-DIHYDROPIRIMIDIN-1 (2H) -IL) -4-FLUORO-3-HIDROXI-4-METHYLETHYDRROFURAN-2-IL) METOXI) (FENOXI) PHOSPHORILAMINE) METHYL PROPANOATE (SOFOSBUVIR)

Country Status (27)

Country Link
US (1) US9340568B2 (en)
EP (1) EP3086795A1 (en)
JP (1) JP2017503015A (en)
KR (1) KR20160099710A (en)
CN (1) CN105873593A (en)
AP (1) AP2016009254A0 (en)
AR (1) AR098929A1 (en)
AU (1) AU2014370299B2 (en)
BR (1) BR112016013714A8 (en)
CA (1) CA2934799A1 (en)
CL (1) CL2016001509A1 (en)
CR (1) CR20160288A (en)
CU (1) CU20160096A7 (en)
DO (1) DOP2016000141A (en)
EA (1) EA201691029A1 (en)
HK (1) HK1222334A1 (en)
IL (1) IL246066A0 (en)
MD (1) MD20160087A2 (en)
MX (2) MX2016008453A (en)
MY (1) MY178102A (en)
PE (1) PE20160750A1 (en)
PH (2) PH12019500372A1 (en)
SG (1) SG11201604818SA (en)
TW (1) TW201609785A (en)
UY (1) UY35917A (en)
WO (1) WO2015099989A1 (en)
ZA (1) ZA201604345B (en)

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SI3154526T1 (en) 2014-06-13 2019-08-30 Ratiopharm Gmbh Solid state forms of sofosbuvir
WO2016023906A1 (en) * 2014-08-13 2016-02-18 Sandoz Ag A crystalline form of sofosbuvir
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WO2016156512A1 (en) * 2015-04-01 2016-10-06 Sandoz Ag A process for preparing a crystalline form of sofosbuvir
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EP3560944A4 (en) * 2016-12-22 2020-08-26 Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. SOLID FORM OF 4'-THIO-2'-FLUORONUCLEOSIDE-PHOSPHAMIDE COMPOUND AND METHOD OF MANUFACTURING THEREOF AND USES THEREOF
RU2656228C9 (en) * 2017-06-13 2019-04-16 Олег Ростиславович Михайлов WEAKLY CRYSTALLISED β-MODIFICATION OF (S)-ISOPROPYL 2-((S)-(((2R,3R,4R,5R)-5-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-(2H)-YL)-4-FLUORO-3-HYDROXY-4-METHYLTETRAHYDROFURAN-2-YL)METHOXY)-(PHENOXY)PHOSPHORYLAMINO)PROPANOATE, METHOD FOR PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITION BASED THEREON
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PE20160750A1 (en) 2016-07-27
EP3086795A1 (en) 2016-11-02
US9340568B2 (en) 2016-05-17
PH12016501203A1 (en) 2016-08-15
DOP2016000141A (en) 2016-07-15
BR112016013714A8 (en) 2020-05-26
UY35917A (en) 2015-05-29
SG11201604818SA (en) 2016-07-28
AU2014370299A1 (en) 2016-06-23
KR20160099710A (en) 2016-08-22
ZA201604345B (en) 2017-11-29
CA2934799A1 (en) 2015-07-02
JP2017503015A (en) 2017-01-26
TW201609785A (en) 2016-03-16
CL2016001509A1 (en) 2016-12-02
MD20160087A2 (en) 2016-12-31
AU2014370299B2 (en) 2017-11-30
BR112016013714A2 (en) 2017-08-08
PH12019500372A1 (en) 2020-03-02
WO2015099989A1 (en) 2015-07-02
HK1222334A1 (en) 2017-06-30
EA201691029A1 (en) 2017-01-30
AP2016009254A0 (en) 2016-06-30
US20150175646A1 (en) 2015-06-25
MY178102A (en) 2020-10-02
PH12016501203B1 (en) 2016-08-15
AR098929A1 (en) 2016-06-22
IL246066A0 (en) 2016-07-31
CN105873593A (en) 2016-08-17
MX2019005253A (en) 2019-08-05
CR20160288A (en) 2016-08-31
MX2016008453A (en) 2016-10-14

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